Palladium-Catalyzed Q-Tube-Assisted Protocol for Synthesizing Diaza-dibenzo[a,e]azulene and Diaza-benzo[a]fluorene Derivatives via O2 Acid-Promoted Cross-Dehydrogenative Coupling.

An appropriate and efficient Q-tube-assisted palladium-catalyzed strategy for the synthesis of novel, unparalleled diaza-dibenzo[a,e]azulene and diaza-benzo[a]fluorene derivatives has been sophisticated, which includes oxygen and AcOH-induced oxidative C(sp3)-C(sp2) cross-dehydrogenative coupling reactions of 1-amino-2-imino-4-arylpyridine-3-carbonitriles with benzocyclic ketones such as benzosuberone, tetralone, thiochromone, and chromone, respectively. This Q-tube gas purging kit assisted-protocol features safe due to easy pressing and sealing, a wide substrate scope, easy workup and purifying phases, and the use of O2 as a benign oxidant, in addition to being scalable and having a high atom economy. The suggested mechanistic pathway includes a formal dehydrative step followed by palladium AcOH-induced CH(sp3)-CH(sp2) oxidative cross-coupling. In this study, X-ray crystallographic analysis has been used to authenticate the targeted products.